Explain the 3 pieces of evidence that disprove Kekule's model of benzene.

Kekulé's model of benzene is that it has 3 double bonds, in a ring of 6 carbons.
One - Benzene isn't very reactive, so if Kekulé's model were to be correct, there would be 3 double bonds in benzene, and so it would react with bromine and decolourise it. It also doesn't do electrophilic addition.Two - The bond lengths in benzene are all the same length. If Kekulé's model was correct, there would be 2 different bond lengths, corresponding to the double bonds and the single bonds in the ring. The actual bond length is between the single and double bond length of carbon.Three - the hydrogenation enthalpy of benzene is expected to be three times that of cyclohexene, if it were Kekulé's model. However, it is smaller, and less energy is produced than expected, meaning that the actual model of benzene is a lot more stable than Kekulé's model.
The correct model for benzene is the delocalised model.

Answered by Ellie W. Chemistry tutor

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